EP1077605A1 - Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles - Google Patents

Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles

Info

Publication number
EP1077605A1
EP1077605A1 EP99923148A EP99923148A EP1077605A1 EP 1077605 A1 EP1077605 A1 EP 1077605A1 EP 99923148 A EP99923148 A EP 99923148A EP 99923148 A EP99923148 A EP 99923148A EP 1077605 A1 EP1077605 A1 EP 1077605A1
Authority
EP
European Patent Office
Prior art keywords
herbicide
surfactant
composition
water
granules
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99923148A
Other languages
German (de)
English (en)
Inventor
George B. Beestman
Jerry M. Green
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP1077605A1 publication Critical patent/EP1077605A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants

Definitions

  • This invention pertains to herbicidal compositions having included therein surfactants that can enhance the biological activity of low dose herbicides and can be formulated in a dry form.
  • Herbicides are used to control unwanted plant vegetation and are widely recognized as essential components in the efficient production of food. It is desirable to keep the herbicide rates low to minimize cost and to minimize adverse environmental effects caused by off-target movements or residues left in the crop or soil.
  • Adjuvants for Agrichemicals, CRC Press, Boca Raton. These adjuvants can be included in the herbicide formulation or can be added to the spray mixture. Adjuvants that increase biological activity include certain crop oil concentrates, certain surfactants, and certain ammonium-based inorganic salts or fertilizer. The oil in the crop oil concentrate adjuvants can be vegetable oil, modified vegetable oil (usually esters or salts of fatty acids), or mineral (petroleum) oils. Adjuvants allow herbicides to be used at low rates and allow control of more species than if the herbicide was used alone. This effect is described by Green, J. M. and Green, J. H. (1993): Weed Technology 7:633-640.
  • Adjuvants are used at various dosages depending on adjuvant type and standard practices, which vary by geographical location. For example, use recommendations for crop oil concentrate adjuvants most commonly range from 0.5% to 1% of the spray volume. The 0.5% concentration is common in Europe and 1% is common in the U.S. with some label recommendations as high as 2%. When added directly to the spray tank, certain surfactants are used at 0.25% of the spray volume in the U.S. and as low as 0.1% in Europe. The surfactant and crop oil concentrate adjuvants currently in use are liquids or low melting solids that are incompatible with dry herbicide formulations and must be packaged separately. In the U.S., ammonium fertilizers are commonly used as adjuvants to enhance herbicide activity at concentrations of 2 to 4% of spray volume.
  • This invention concerns a herbicidal composition
  • a herbicidal composition comprising at least one low-dose herbicide; at least one surfactant selected from Formulae I, II and III including stereoisomers,
  • each of R, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of H, M or (CH 2 CH 2 O) x CH2(CH2) y CH3;
  • This invention pertains to the use of certain alkyl ether citrate, tartrate and adipate surfactants for enhancing biological activity of low-dose agricultural herbicides.
  • a low-dose herbicide is defined in the context of this disclosure to be a herbicide that is efficacious for control of undesired vegetation at application rates of less than 100 g a.i./ha.
  • the alkyl ether citrate, tartrate or adipate compounds of Formula I, II or III provide a high unit activity to these herbicides compared to the same agricultural herbicides applied alone.
  • These surfactants surprisingly provide the enhanced biological effect at doses lower than is generally needed with common surfactants.
  • the surfactants of Formula I, II or III are remarkably effective, they can be included in formulated compositions of low-dose herbicides in sufficient amount to enhance the biological effect without the grower or farmer needing to add additional adjuvants to the spray tank.
  • Certain salts and certain highly ethoxylated forms of the surfactants of Formula I, II, or III are solids and therefore particularly useful in solid types of formulations.
  • the low-dose herbicide is selected from acetolactate synthase inhibiting herbicides, protoporphyrinogen oxidase inhibiting herbicides, /7-hydroxyphenylpyruvate deoxygenase inhibiting herbicides, and combinations thereof. More preferred is the composition wherein the low-dose herbicide is an acetolactate synthase inhibiting herbicide. Most preferred is the composition wherein the acetolactate synthase-inhibiting herbicide is selected from the group consisting of thifensulfuron-methyl, rimsulfuron and nicosulfuron; and mixtures thereof.
  • Preferred is a composition composed of herbicide granules and surfactant granules, the herbicide and optionally at least one additive comprising the herbicide granules; and at least one compound selected from Formula I, II and III, and optionally at least one additive comprising the surfactant granules.
  • composition wherein the surfactant is of Formula I. More preferred is the composition wherein the surfactant is of Formula la, lb or Ic: O
  • Ic wherein x is 17, y is an integer 14 to 16, and M is K + , Na + or NH,4 + .
  • the concentration of the at least one surfactant and any adjuvant additive is about 0.01 to about 0.1% of the spray volume.
  • the mono-ethoxylated surfactants of Formula la, the tri-ethoxylated surfactants of Formula lb and the C ⁇ g alkyl citrate surfactants of Formula Ic are commercially available from Witco Corporation, Greenwich, CT. More generally, surfactants of Formulae I, II and III are prepared by condensing the corresponding free carboxylic acids with CH3(CH 2 ) y O(CH 2 CH2 ⁇ ) x H.
  • the resulting average number of carboxylic acid groups per molecule esterified with CH3(CH2) y O(CH2CH 2 O) x H depends upon the ratio of the number of moles of CH3(CH 2 ) y O(CH CH 2 O) x H to the number of moles of the starting free carboxylic acid.
  • the mole ratio of starting CH3(CH2) y O(CH 2 CH 2 O) x H to free carboxylic acid is about 1 :1.
  • the mole ratio of CH 3 (CH2) y O(CH2CH2 ⁇ ) x H to starting free carboxylic acid is correspondingly increased.
  • the esterification condensation reaction is accelerated by heating and catalysis using strong protic acids, such as phosphoric acid, sulfuric acid, /?-toluenesulfonic acid and sulfonic acid resins, or Lewis acids such as boron trifluoride and butyltin hydroxide oxide hydrate.
  • strong protic acids such as phosphoric acid, sulfuric acid, /?-toluenesulfonic acid and sulfonic acid resins, or Lewis acids such as boron trifluoride and butyltin hydroxide oxide hydrate.
  • Surfactants of Formulae I, II and III can exist as stereoisomers.
  • the various stereoisomers include enantiomers and diastereomers.
  • surfactant properties of stereoisomers are generally similar, some variation is possible between diastereomers.
  • physical properties important to formulations, such as melting points typically differ somewhat between pure enantiomers and racemic mixtures.
  • Racemic mixtures usually, but not always, have higher melting points and lower solubilities than the separated enantiomers.
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the surfactants of Formula I, II and III may be present in the compositions of this invention as a mixture of stereoisomers or as a single stereoisomer. Salts of Formulae I, II and III wherein at least one of R, R 2 , R 3 , R 4 , R 5 , R 6 or R 7 is M are very useful surfactants for this invention, because they are often solids. Each M is independently an organic or inorganic cation.
  • Organic cations include, for example, isopropylammonium, triethylammonium, tetra-n-butylammonium, benzyltrimethylammonium and trimethylsulfonium.
  • Inorganic cations include, for example, lithium, sodium, potassium, calcium, magnesium, barium and ammonium. Sodium, potassium and ammonium are preferred cations for this invention because of their low cost and solid-promoting ability.
  • Salts of Formulae I, II and III wherein at least one of R, R 2 , R 3 , R 4 , R 5 , R 6 or R 7 is M can be prepared by reacting the corresponding acid forms of Formulae I, II and III with amines (e.g., treatment with triethylamine to give the triethylammonium salt) or with bases such as hydrides, hydroxides, alkoxides or carbonates of lithium, sodium, potassium, calcium, magnesium, barium or quaternary ammonium.
  • Ammonium salts can be prepared by treatment with anhydrous ammonia or ammonia dissolved in water (i.e. ammonium hydroxide).
  • the desired effect of enhancement of herbicide activity may be obtained by use of at least one of the citrate, tartrate, or adipate based surfactants of Formula I, II or III, by a combination thereof, or by a combination of said citrate, tartrate, or adipate based surfactants of Formula I, II or III with one or more other adjuvants known to enhance herbicidal activity.
  • Preferred low-dose herbicides of the present invention are selected from the group consisting of acetolactate synthase inhibiting herbicides, protoporphyrinogen oxidase inhibiting herbicides, -hydroxyphenylpyruvate deoxygenase inhibiting herbicides, and combinations thereof.
  • Acetolactate synthase inhibiting herbicides include sulfonylureas (and derivatives such as sulfamoylureas), such as amidosulfuron, azimsulfuron, bensulfuron- methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron- methyl, ethoxysulfuron, fiupyrsulfuron methyl, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron
  • protoporphyrinogen oxidase inhibiting herbicides include include azafenidin, carfentrazone-ethyl, flumiclorac-pentyl, flumioxazin, fluthiacet-methyl, oxadiazon, oxadiargyl, pyraflufen-ethyl, sulfentrazone and (6S-cw)-l-chloro-N-[2-chloro- 4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH-pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]- methanesulfonamide, and the agriculturally suitable salts of any of the foregoing.
  • Examples of ?-hydroxyphenylpyruvate deoxygenase inhibiting herbicides include sulcotrione, isoxaflutole, and 2-[4-(methylsulfonyl)-2-nitrobenzoyl]-l,3-cyclohexanedione (mesotrione), and the agriculturally suitable salts of any of the foregoing.
  • Some of the aforementioned low-dose herbicides inhibiting acetolactate synthase, protoporphyringen oxidase or ⁇ -hydroxyphenylpyruvate deoxygenase can be present in the compositions of the present invention in the form of their agriculturally suitable salts.
  • agriculturally suitable salts include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, adipic, butyric, citric, fumaric, lactic, maleic, malonic, oxalic, proprionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, adipic, butyric, citric, fumaric, lactic, maleic, malonic, oxalic, proprionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • agriculturally suitable salts include those formed with amine bases (e.g., pyridine, ammonia or triethylamine) or metallic or quaternary ammonium bases (e.g., hydrides, hydroxides, alkoxides or carbonates of lithium, sodium, potassium, calcium, magnesium, barium or quaternary ammonium).
  • amine bases e.g., pyridine, ammonia or triethylamine
  • metallic or quaternary ammonium bases e.g., hydrides, hydroxides, alkoxides or carbonates of lithium, sodium, potassium, calcium, magnesium, barium or quaternary ammonium.
  • Particularly useful salts include the lithium, sodium, potassium, triethylammonium, and quaternary ammonium salts such as tetra- ⁇ -butylammonium and benzyltrimethylammonium.
  • WO 97/15576 The synthesis involves the reaction of ( ⁇ R-trans)- 1 -chloro-N-[2-chloro-4-fluoro-5-(tetrahydro-6-hydroxy- 1 ,3-dioxo- lH-pyrrolo[l ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide with diethylaminosulfur trifluoride (DAST) in dichloromethane solution.
  • DAST diethylaminosulfur trifluoride
  • the compound 2-[4-(methylsulfonyl)-2- nitrobenzoyl]-l,3-cyclohexanedione can be prepared as described in U.S. 5,006,158.
  • the synthesis involves rearrangement of 3-oxo-l-cyclohexen-l-yl 4-(methylsulfonyl)-2- nitrobenzoate in the presence of acetone cyanohydrin and triethylamine in acetonitrile.
  • Flucarbazone can be prepared as described in U.S. 5,534,486.
  • the synthesis involves the reaction of 2-(trifluoromethoxy)benzenesulfonyl isocyanate with 2,4-dihydro-5-methoxy-4- methyl-3H-l,2,4-triazol-3-one.
  • U.S. 5,550,244 describes an alternative coupling method.
  • the ratio of concentration of surfactants to herbicides ranges from about 1.5:1 to about 150:1 by weight. These ratios refer to the total weight of surfactants of Formulae I, II and III compared to the total weight of low-dose herbicide active ingredients. Preferred is a ratio of about 2: 1 to about 40: 1. More preferred is about 4: 1 to about 35:1. Even more preferred is about 5 : 1 to about 30:1. Most preferred is about 10:1.
  • composition of the present invention can be used alone or in combination with other commercial herbicides.
  • the composition of the present invention can also comprise one or more high-dose herbicide active ingredients in addition to the low-dose herbicide active ingredient or ingredients.
  • a mixture with one or more of the following herbicides may be particularly useful for weed control: acifluorfen, anilofos, asulam, atrazine, bentazon, bromacil, bromoxynil, hydroxybenzonitrile, chloramben, chloroxuron, chlortoluron, cyanazine, dazomet, desmedipham, dicamba, dichlobenil, dichlorprop, diphenamid, dipropetryn, diuron, fenac, fenuron, fluometuron, fluridone, fomesafen, glyphosate acid or its corresponding salts especially the isopropylamine, sodium, potassium, ammonium and trimesium salts, hexazinone, ioxynil,
  • compositions of the present invention may include at least one additive, such as a drying agent, a dispersant, an anti-caking agent, an anti-foaming agent, a wetting agent, a chemical stabilizer, a diluent, and other types of adjuvants.
  • a drying agent such as a drying agent, a dispersant, an anti-caking agent, an anti-foaming agent, a wetting agent, a chemical stabilizer, a diluent, and other types of adjuvants.
  • a drying agent such as a drying agent, a dispersant, an anti-caking agent, an anti-foaming agent, a wetting agent, a chemical stabilizer, a diluent, and other types of adjuvants.
  • a drying agent such as a drying agent, a dispersant, an anti-caking agent, an anti-foaming agent, a wetting agent, a chemical stabilizer, a diluent,
  • Water-soluble drying agents include but are not limited to sodium, calcium and ammonium salts of ligninsulfonates (optionally polyethoxylated); salts of maleic anhydride copolymers, salts of polyacrylic acids, salts of condensed phenolsulfonic acids, salts of the napthalene sulfonate-formaldehyde condensates, polyvinylpyrrolidone, polyvinylalcohol, polyethylene oxide, and co-polymers of these.
  • Water-insoluble drying agents include but are not limited to clays, synthetic and diatomaceous silicas, calcium and magnesium silicates, titanium dioxide, and charcoal. Useful levels include up to about 70% by weight.
  • Adjuvants include but are not limited to other surfactants, oil concentrates, alkyl sulfosuccinates, taurates, alkyl sulfate and phosphate esters, acetylenic diols, ethoxyfluorinated alcohols, ethoxylated silicones and alkyl phenol ethoxylates, as well as organic sulfonates and alcohol ethoxylates. If an adjuvant is used, useful levels include up to about 10%) by weight.
  • Anticaking agents to prevent clumping of granules stored under hot warehouse conditions include but are not limited to sodium and ammonium phosphates, sodium acetate, sodium metasilicate, magnesium, zinc and calcium sulfates, magnesium hydroxide, (all optionally as hydrates), anhydrous calcium chloride, molecular sieves, sodium alkylsulfosuccinates, calcium and barium oxides. If anticaking agent is needed, useful levels include up to about 10% by weight.
  • Chemical stabilizers to prevent decomposition of active ingredient during storage include but are not limited to sulfates of alkaline earths and transition metals such as magnesium, zinc, aluminum and iron; lithium, sodium and potassium phosphates; calcium chloride and oxide; and, boric anhydride. If chemical stabilizer is needed, useful levels include up to about 10% by weight.
  • Diluents may be water-soluble or water-insoluble.
  • the water-soluble diluents may be salts, surfactants or carbohydrates which dissolve rapidly in water; non-limiting examples include sulfates of sodium, potassium, magnesium and zinc, sodium and potassium chloride, gelatin, urea, sugar, sorbitol, sodium benzoate, lactose, and alkali metal and alkali earth phosphates.
  • Water-insoluble diluents include but are not limited to starch, modified starch, cyclodextrin, aluminum, calcium and zinc oxide, calcium and magnesium carbonate, sodium, potassium, calcium and barium sulfate. Water-soluble diluents are preferred. If diluent is needed, levels up to about 40%) by weight may be included.
  • Anti-foaming agents include but are not limited to stearates, silicones, and ethoxylates of HLB (Hydrophobic/Lipophilic Balance) values less than about 5.
  • HLB Hydrophilic Balance
  • the formulations are dry formulations including dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Most preferred are granule or pellet type formulations.
  • Conventional granulation methods for preparing granule compositions involve (1) water-spraying in fluidized bed or pan granulation equipment, (2) spray-drying, (3) extrusion of a water- wet paste, and (4) dry compaction or (5) melt extrusion.
  • the surfactant, herbicide and optionally at least one additive can be granulated together to provide granules comprising both the herbicide and the surfactant.
  • the surfactant can be separately granulated prior to combination with the herbicide.
  • the at least one surfactant of Formula I, II or III and optionally at least one additive, as described above can be granulated to form a surfactant granule
  • the herbicide and optionally at least one additive, as described above can be granulated to form a herbicide granule.
  • the surfactant granules and the herbicide granules can then be combined and applied and/or packaged together, or packaged and/or applied separately.
  • the present invention further concerns a method for controlling the growth of undesired vegetation which comprises adding the herbicidal composition described above to water and applying to the locus to be protected an effective amount of the herbicidal composition which is soluble or dispersible in the water.
  • the amount of surfactant and any adjuvant additive in the water is about 0.01 to about 0.1% weight or volume per volume of water.
  • Application of the herbicidal composition can be by spraying. In spraying applications, the amount of surfactant and any adjuvant additive would preferably be about 0.01 to about 0.1% of the spray volume expressed either on a weight or volume basis.
  • Typical spray volumes range from as low as about 10 L/ha in aerial application up to about 500 L/ha in ground application.
  • This Reference Example illustrates a general method for preparing surfactants useful for this invention.
  • EXAMPLE 1 The effect of Compounds 1-7 on the activity of nicosulfuron was investigated by tank mixing the compounds with the herbicide and compared with the activity of three commercial surfactants at the same rates. Evaluation of the compounds in Table 1 was made by mixing the compound with a nicosulfuron solution and spraying the resulting solution at a rate of 3.5 g /ha nicosulfuron in a spray volume of 187 L/ha on giant foxtail (Setariafaberi). Adjuvant dose is expressed on a weight basis as a % concentration of the spray volume. Four replications were made of each treatment. Plants were evaluated after two weeks by measuring their green fresh weights and converting these weight by comparison to an untreated control treatment into percent control values.
  • Trend® 90 surfactant is 90% nonionic surfactant (isodecyl alcohol ethoxylate) sold by Du Pont de Nemours (France) S. A., 137 rue de l'Universite, 75334 Paris, France.
  • Agridex® nonionic spray adjuvant is a crop oil concentrate (83%> paraffin base petroleum oil and 17%) surfactant emulsifiers) sold by Helena Chemicals Co., 5100 Poplar Ave., Memphis, TN 38137.
  • Scoil® is a modified vegetable oil concentrate (mixture of methylated seed oil and surfactant emulsifiers) sold by Agsco, Inc., Mill Road, Grand Forks, ND 58206.
  • EXAMPLE 2 The effect of Compounds 1-7 on the activity of nicosulfuron was investigated by tank mixing the compounds with the herbicide and compared with the activity of two commercial surfactants at the same rates. Evaluation of the compounds in Table 2 was made by mixing the compound with a nicosulfuron solution and spraying the resulting solution at a rate of 3.5 g/ha nicosulfuron in a spray volume of 187 L/ha on giant foxtail (Setariafaberi). Six replications were made of each treatment. Plants were evaluated after two weeks by measuring their green fresh weights and converting these weight by comparison to an untreated control treatment into percent control values.
  • EXAMPLE 3 A dry high concentration water-soluble granule formulation was prepared based upon a water-soluble drying agent/dispersant. These granules can subsequently be blended with herbicide dispersible granule formulations to produce herbicide/surfactant blends in all desired proportions.
  • Reax® 85A sodium lignin sulfonate produced by Westvaco 50%
  • lignosulfonate and alkylether citrate surfactant were dissolved in water and then dried in a vacuum oven. Resultant cake was milled to a powder, moistened, extruded, dried and broken to desired granule length.
  • aqueous solution moistened, extruded, dried and broken to desired granule length.
  • Other water soluble polymers such as acrylic-based, naphthalene-based, and pyrrolidone-based polymers may be used as drying agents or carriers for these alkylether citrates.
  • a dry high concentration water-dispersible granule formulation can be prepared based upon a water-insoluble drying agent. These granules can subsequently be blended with herbicide water-dispersible granule formulations to produce herbicide/surfactant blends in all desired proportions.
  • Sipernat® 50S (a synthetic silica manufactured by Degussa Corp) 25%
  • Aerosol® OTB (dioctylsulfosuccinate wetting agent manufactured 5%> by Cytec Industries, Inc.)
  • Foamaster® Soap L (tallowate anti-foam made by Henkel Corp.) 2%
  • Morwet® D425 (condensed naphthalene sulfonate dispersant 5% manufactured by Witco Corp.)
  • Silica and citrate surfactant are combined by high shear mixing to form a powder. Other components are added, blended and milled to finer than 150 microns. The milled powder is moistened to an extrudable paste, extruded, dried, and broken to desired length granules.
  • a dry salt form of an acid citrate surfactant can be prepared that can be processed to granules without a drying agent. These granules can subsequently be blended with herbicide dispersible granule formulations to produce herbicide/surfactant blends in all desired proportions.
  • the salt is milled to less than 150 microns, moistened to an extrudable past, extruded, dried, and broken to desired granule length.
  • Example 3 was repeated using Compound 1 in place of Compound 6.
  • Example 4 was repeated using Compound 4 in place of Compound 6.
  • EXAMPLE 12 This is an example of a wettable powder formulation of a surfactant that can subsequently be used to formulate a herbicide product.
  • Siperonat® 50S (a synthetic silica manufactured by Degussa) 25%>
  • Aerosol® OTB (dioctylsulfosuccinate made by Cytec Industries) 5%
  • Foamaster® Soap L sodium tallowate made by Henkel
  • Morwet® D425 (condensed naphthalene sulfonate manufactured 5% by Witco Corporation)
  • EXAMPLE 13 A formulation containing the solid salt form of the surfactant and herbicides in the same composition can be prepared.
  • EXAMPLE 14 A formulation containing the surfactant in a water-soluble drying agent and herbicides in the same composition can be prepared.
  • Igepon® T77 sodium N-methyl-N-oleoyl taurate, manufactured by 5% Rhodia
  • Agrimer® 15 polyvinylpyrrolidone, manufactured by ISP
  • the ingredients are blended, milled, moistened, extruded, dried and broken to desired granule length.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne l'utilisation de certains tensioactifs de citrate, de tartrate ou d'adipate d'alkyléther afin d'augmenter l'activité biologique d'herbicides agricoles.
EP99923148A 1998-05-18 1999-05-17 Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles Withdrawn EP1077605A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US8580198P 1998-05-18 1998-05-18
US85801P 1998-05-18
PCT/US1999/010857 WO1999059406A1 (fr) 1998-05-18 1999-05-17 Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles

Publications (1)

Publication Number Publication Date
EP1077605A1 true EP1077605A1 (fr) 2001-02-28

Family

ID=22194039

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99923148A Withdrawn EP1077605A1 (fr) 1998-05-18 1999-05-17 Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles

Country Status (4)

Country Link
EP (1) EP1077605A1 (fr)
AU (1) AU3998499A (fr)
CA (1) CA2328479A1 (fr)
WO (1) WO1999059406A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9823010D0 (en) 1998-10-22 1998-12-16 Agrevo Uk Ltd Critic acid derivates
US6423376B1 (en) * 2000-04-06 2002-07-23 Air Products And Chemicals, Inc. Tartaric acid diesters as biodegradable surfactants
JP4839558B2 (ja) * 2001-09-26 2011-12-21 住友化学株式会社 顆粒状水和剤
AR048414A1 (es) * 2004-02-26 2006-04-26 Ishihara Sangyo Kaisha Composicion herbicida
JP2005272442A (ja) * 2004-02-26 2005-10-06 Ishihara Sangyo Kaisha Ltd 除草組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1201411B (it) * 1985-03-26 1989-02-02 Rol Raffineria Olii Lubrifican Tesnioattivi derivati dall'acido citrico
IT1187714B (it) * 1985-07-26 1987-12-23 Rol Raffineria Olii Lubrifican Tenisoattivi derivati da idrossiacidi bicarbossilici
HU206241B (en) * 1989-05-08 1992-10-28 Chinoin Gyogyszer Es Vegyeszet Plant protective and additive compositions comprising citric acid and tartaric acid derivatives and process for producing veterinary compositions
US5521144A (en) * 1992-09-18 1996-05-28 Central Soya Company, Inc. Herbicide composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9959406A1 *

Also Published As

Publication number Publication date
AU3998499A (en) 1999-12-06
CA2328479A1 (fr) 1999-11-25
WO1999059406A1 (fr) 1999-11-25

Similar Documents

Publication Publication Date Title
US8877244B2 (en) Stabilized pesticidal granules
EP0647096B1 (fr) Compositions agricoles contenant des esters liquides de fluroxypyr
CN112998022A (zh) 一种含三唑磺草酮的除草组合物及其应用
BRPI0710376A2 (pt) mistura, composição herbicida e método de controle da vegetação indesejada
EP1365649B1 (fr) Combinaison d'herbicide-phytoprotecteur a base de phytoprotecteurs isoxazoline carboxylate
CN115462385A (zh) 一种包含具有旋光活性的苯基异噁唑啉类的除草组合物及应用
WO2004023876A1 (fr) Procede de preparation de compositions sulfonamides extrudees a partir d'une pate
US20070123426A1 (en) Mixtures
US6852674B2 (en) Herbicidal mixture comprising a benzoyl derivative, a fertilizer containing nitrogen and an adjuvant
EP0968649A1 (fr) Adjuvants pour compositions herbicides solides
HU225390B1 (en) Sulphonyl urea and adjuvant based solid mixtures
JP2004346030A (ja) 薬害軽減剤及びその利用
CN115707690A (zh) 一种3-异恶唑烷酮类化合物及其制备方法、除草组合物和应用
EP1077605A1 (fr) Tensioactifs de citrate, de tartrate ou d'adipate d'alkylether et leur utilisation dans des formulations agricoles
CA2214387C (fr) Formulations solides et stables d'herbicides a base de cyclohexenonoximether
CN112745305A (zh) 一种三嗪酮类化合物及其用途
CA3088620A1 (fr) Melanges herbicides
CA2534020C (fr) Composition auxiliaire de formulation agrochimique et ses utilisations
EP4008185A1 (fr) Composition herbicide comprenant des microparticules de saflufenacil
CN112625035B (zh) 一种5-氯苯并噁唑衍生物或其作为农药可接受的盐、组合物及其用途
EP3888461A1 (fr) Dispersions non aqueuses comprenant des inhibiteurs de dioxygénase hydroxyphénylpyruvate et de l'acide citrique
WO2024099118A1 (fr) Composés oxabicycloalcane, leur procédé de préparation, composition herbicide et utilisation associée
WO2024073018A1 (fr) Microparticules biodégradables pour réduire la volatilité de la bixolozone
CN117882729A (zh) 一种含环己烷-1，3-二酮衍生物的除草剂组合物及其应用
WO2023110491A1 (fr) Procédé de régulation de la végétation indésirable dans un environnement aquatique

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20001026

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB IT

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 20011120